American writer, playwright, and contrarian Gore Vidaldied of complications from pneumonia at his Hollywood home Tuesday night. He was 86. Since his first play, Visit to a Small Planet, debuted in 1957, TIME has been covering Vidal extensively — our archives include nearly 30 reviews or essays on his influence. And although the first reviewer did not care for the playwriting as much as the acting in Visit‘s “kind of vaudeville show,” it marked the beginning of a long public fascination with the man who would become one of the country’s preeminent minds. Here, assembled for your reading pleasure, is a small sampling of TIME’s meditations on Vidal:

The Best Man (1960)

But Playwright Vidal knows that to keep things spinning, storytelling means more than anecdote-mongering, and a protagonist more than a prototype. The Best Man provides little about issues or rival parties; indeed it all but obliterates the idea of there being any second party… A modern-angled political morality play, it yet never forgets that bad politics make good theater, that stage tricks pale beside political ones. — Apr. 11, 1960

Myra Breckinridge (1968)

Is the Olympia Press alive and publishing in Boston? Has literary decency fallen so low—or has fashionable camp risen that high?

This novel brings up such questions because Gore Vidal is a reasonably serious writer: his credentials, if haphazard, are all in order. Although he has taken time out to run for Congress as a Democrat in 1960 and to haunt television panels as a sort of sexy Schlesinger or political Capote, he has always been primarily a working novelist (Julian), playwright (Visit to a Small Planet), and critic (Rocking the Boat).

Nothing in the versatile Vidal’s past will quite prepare the reader for Myra Breckinridge. Vidal and his publisher, insisting that the sexual problems of the title character represent a suspense element vital to the novel’s enjoyment, coquettishly plead that the book not be reviewed at all. — Feb. 16, 1968

Put a toga and a wreath on Gore Vidal and he could pass as a Roman at Nero’s court. You know, the cheerfully disillusioned fellow in the corner who always said the empire would come to a bad end and—now that the fire has started—is absolutely the life of the party.

Nobody can beat the exhilaration of a pessimist who thinks the end-time has come. Writing slightly bad-tasting novels (Myra Breckinridge) and bland-tasting plays (Visit to a Small Planet) is just the start for Vidal. He keeps busy as an opinion maker, staging shoot-outs with William Buckley on TV and churning out some of the liveliest doomsday journalism ever, mostly in today’s essay form, the book review. — Mar. 28, 1969

Burr (1973)

It will be especially galling to those who hate and envy Gore Vidal to pick up Burr and discover that the gods of Julian the Apostate once again seem to have smiled broadly in his direction. — Nov. 05, 1973

1876 (1976)

Vidal obviously numbers himself among this Sisyphean elite.

His tone is that of the seer scorned; yet he can hardly claim to be the prophet ignored. For 30 years he has been a cinder in the public eye: novelist, Broadway playwright, television dramatist, screenwriter, essayist, congressional candidate, actor, troubador to the Kennedy Camelot, talk-show regular, political debater and full-time nag. Millions who have never read him recognize his electronic presence: elegance bordering on narcissism, feline languor, throaty self-assurance.

He has never lacked a podium to argue his pet causes—and to infuriate great masses of his countrymen at will. He has mocked the “heterosexual dictatorship” in the U.S., championed the rights and pleasures of homosexuals, and called for a legal curb on human breeding. He has castigated America as “the land of the dull and the home of the literal” and repeatedly predicted the “smashup” of the “last empire on earth.” Like many a gadfly before him, from Twain to Mencken, Vidal has won fame and wealth by biting the land that feeds him. — Mar. 01, 1976

Somewhere along the way, Vidal seems to have grown weary of his lonely stand against the barbarians. The more he castigated them, the more they praised and purchased his witty and iconoclastic novels. Myra Breckinridge (1968) was supposed to be a poke in the eye to smug notions of sexual identity; it became a bestseller instead. Julian (1964) and Burr (1973) insisted that true heroes of history are villains in the dull popular imagination; millions of people, including dullards, relished this insight. By this time, success dogged Vidal at every turn. If you cannot offend your enemies, why not take it easy and join them? So, here comes Lincoln, a massive package bearing every wretched excess that Vidal so justifiably scorned eleven years ago. — May 21, 1984

Palimpsest (1995)

In a lovely passage, Vidal says he learned from his grandfather ”the ability to detect the false notes in those arias that our shepherds lull their sheep with”–and in fact his story sparkles when he deftly exposes the hypocrisies of Hollywood and Washington. As a writer he is at his best as an uncompromising critic, and at one point turns his sensibility on himself with sharp-eyed accuracy: ”In this text,” he writes, “I am not moving toward anything that I am aware of.” — Richard Stengel, Oct. 09, 1995

The Golden Age (2000)

A novelist who puts himself into his story is either a Postmodernist or uncommonly vain. Vidal is not a Postmodernist, but he probably deserves a place in his chronicle. He knew or met a number of the real, historical people–Eleanor Roosevelt, Joseph Alsop, Tennessee Williams–who move through the pages of The Golden Age. He has been, for the past half-century, an uncommonly public literary figure: a near ubiquitous television guest and, twice, an unsuccessful candidate for elective office. Living well is Vidal’s revenge, which he does much of each year at La Rondinaia, his spectacular house in Ravello perched 200 ft. above the Amalfi coast. His mornings are customarily spent writing in a room filled with leatherbound copies of all his books and framed magazine covers bearing his face. — Paul Gray and Curtis Ellis, Sept. 25, 2000